DE709689C - Process for the production of acidic dyes of the anthraquinone series - Google Patents

Description

GERMAN EMPIRE

ISSUED AUGUST 23, 1941

REICH PATENT OFFICE

PATENT LETTERING

. JVr 709689 CLASS 22B GROUP 3 02

C 52251 IVd / 22 b

Dr. Ernst Gutzwiller in Basel, Switzerland,

has been mentioned as the inventor.

Sandoz A.-G. in Basel, Switzerland Process for the production of acidic dyes of the anthraquinone series

Patented in the German Reich on December 5, 1936 Patent granted July 17, 1941

The priority of the application in Switzerland of January 27, 1936 is "claimed.

It has been found that new dyes of the anthraquinone series differ from the general composition

^N <:

CO

-SO ₃ H

W ¹ V

NH-A —SO., ·

NH-D

wherein R ₁ and R _{2 are} hydrogen or alkyl, A is a substituted or unsubstituted benzene radical, D is an oxyalkyl radical and X is hydrogen or any substituent

tuenten mean to be obtained if one anthraquinone derivatives of the general composition

R ₁

^{N <}

V i

halogen

wherein R ₁ and R _{2 are} hydrogen or alkyl, Y is a halogen or sulfonic acid group and X is hydrogen or any substituent, with aminobenzene

Example ι

5 parts of i-iiniino ^ -bromoanthraquinone-j-sulphonic acid sodium, 25 parts of sodium bicarbonate, 20 parts of i-aminobenznl-3-sulphonic acid ethniolate

(H. X - _C; Hi - SO, - C II N, O II H _1,

Part of copper powder and 600 parts of water are ^{stirred at 50 to 100 J} until the reaction has ended. The dye formed can be separated off by filtration. The copper-free dye can be cleaned by falling over from hot, dilute, acidified saline solution. He dyes wool from an acid bath in beautiful red-red-blue shades.

Instead of i-aminobenzene-3-sulfonic acid ethanolamide i-aminobenzene-2- or -4-sulfonic acid ethanolamide can also be used Find. Furthermore, the benzene residue can still be substituted.

Example 2

2 ·, parts of i-amino-4-bronianthraquinone-J-sulfonic acid sodium, 1 2 parts of sodium bicarbonate

sulfonsäuremonooxyalkylamiden condensed and the condensation compounds in which Y represents halogen, - treated for the purpose of introducing the sulfonic acid group in the / i-position with sulfites. * '■ $$%?

The dyes obtained in this way are suitable ®κϊϊ ^ |. for dyeing deep fibers. onStfe They also draw from neutral baths, especially for dyeing wool from acidic Bath, and are characterized by their lively hue and good leveling power.

These dyes are produced in the usual way, often with an advantage is, in the presence of organic solution

'' 5 to work medium and in an indifferent atmosphere. The condensation temperature can can also be changed within wide limits. If the starting compounds are the / j-halogenated Use anthraquinone derivatives

ao det, the / Mlnlngenatrim by heating with sulfites in the usual way against a Sulfonsiuircgrupp according ert'olgter Kundensation: exchanged ^1, wherein iniin operates with advantage under pressure and at elevated temperature.

? -5 Compared to the next comparable dyes known from German patent specification 55S764, example 6, and French patent specification 707671, example 2, the new dyes have either greater vividness of the color shade, better chromium fastness, improved lightfastness or better leveling capacity on.

nat, 18 parts
Fonsäureäthanolamid, 1 part of copper powder and 300 parts of water are stirred at up to 65 ° until the dye formation, ndebjst. The substance precipitated in crystals is filtered and removed from the copper. By falling over from hot, dilute, acidified saline solution, the pure dye can be obtained in beautiful crystals. He dyes wool from an acid bath in vivid blue tones.

• Instead of the ethanolamide, the corresponding propanol or butanol or IVopandiolamide find use, where the corresponding dyes are obtained.

Example 3 10 parts of i-amino-2, 4-dibromoanthraquinone,

15 parts of ι. \ Mino-4-methylbenzene-3-sulfonsäureäthauolamid, 5 parts of potassium acetate and 0.3 part of copper acetate are in the presence of a suitable solvent such as nitrobenzene or dimethylaniline, ^{heated to 120 to 150 0} until the condensation no longer continues to progress. The base is separated in a conventional manner and preferably treated with sulfites in the presence of phenol, at temperatures of 100 to 150 ^0th The water-soluble dye obtained is identical to the dye obtained according to Example 2.

Claims (1)

Claim: Process for the preparation of acidic dyes of the anthracliiiion series, thereby characterized that one AnthraehinonaljJlE ^ rtnlinge of the general / composition ^ R ₁ X - CO ' halogen wherein R ₁ and R _{2 are} hydrogen or alkyl, Y is a halogen or a sulfonic acid group and X is hydrogen or any substitute, condensed with aminobenzene sulfonic acid monooxalkylamides and the condensation compounds in which Y is halogen, for the purpose of introducing the. Treated sulfonic acid group in the / J position with SuI-fiten.